


Stuck At the End of Cupid's Arrow

by Fandom_Stuff



Category: Supernatural
Genre: Angels, Angst, Cupids, Dean and Cas are destined to be together, Drunken fluff, Love, M/M, but neither will take the first step, eleven years of
Language: English
Status: Completed
Published: 2020-06-19
Updated: 2020-06-19
Packaged: 2021-03-03 23:07:27
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,789
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24813556
Author URL: https://archiveofourown.org/users/Fandom_Stuff/pseuds/Fandom_Stuff
Summary: Cupid has never been more frustrated in all the millennia that he's been alive. Dean Winchester and Castiel were supposed to be an easy assignment, they're clearly in love, anyone can see it, but the two idiots absolutely REFUSED to admit it to each other and no matter what Cupid tried, he couldn't get them to.After eleven years, he finally decides to enlist some help and Sam Winchester seems to be the perfect person to call. Between the two of them they should be able to get a love confession out of the angel and the hunter. Right?... RIGHT!?One can only hope.
Relationships: Castiel/Dean Winchester, Dean Winchester/Castiel, Destiel
Comments: 6
Kudos: 63





	Stuck At the End of Cupid's Arrow

**Author's Note:**

  * For [make_your_user_a_name](https://archiveofourown.org/users/make_your_user_a_name/gifts).



> This idea is from tearsofgrace's post on [Tumblr](https://classicallysuperwholock.tumblr.com/post/620401648148398080/fic-where-the-main-character-is-the-cupid-assigned)  
> Here's the prompt:
> 
> fic where the main character is the cupid assigned dean/cas’ case and they just get increasingly frustrated trying to get them together  
> “Not for nothing, but last time someone looked at me like that, I got laid.” (okay okay it’s been a while but we got there... wait...)  
> “Sorry, but I’d rather have you. Cursed or not.” (you’re actually in love can you please just admit it so I can go home)  
> “I need you.” (c’mon dean just say it.... ugh and he’s gone)  
> “I prayed to you, Cas. Every night.” (*unintelligable screaming*)  
> “I’m not leaving here without you.” (cas if you don’t go with him i swear to chuck)  
> “Lose the vest. C’mon, just lose the vest.” (what is wrong with you. what. I can’t. I literally cannot make this any easier for you)  
> “I love you. I love all of you.” (HE WAS LOOKING RIGHT AT YOU GODDAMNIT ARE YOU THIS DENSE???)  
> “I forgive you, of course I forgive you.” (I want to be hopeful, but... it’s been 10 years. I’m so tired eventually the cupid appears to sam like, look dude. you gotta help me.
> 
> I hope I do this justice, I'm a bit iffy on if it came out well or not.

Cupid let out a sigh as he watched his latest assignment once again fail to fall in love. Dean Winchester and Angel of Heaven, Castiel, were the toughest case that he’d ever been assigned. He couldn’t quite remember the last time an angel and a human were meant to be with each other for the rest of their lives, but this was certainly the first time he’d been assigned such a case. 

It wasn’t that they didn’t love each other, anyone could see that they did, and having already touched both of them to mark their hearts, they clearly had to be in love, but it was that neither of them wanted to  _ admit  _ it. 

There had been quite a few times over the years, yes  _ years _ , that’s how long he’d been at this, where he’d thought he was close. He remembered a time where Dean had so blatantly flirted with Castiel, even saying that, “the last time someone looked at me like that, I got laid.” If that wasn’t a  _ direct  _ invitation to Castiel, then he didn’t know what was. The problem was that Castiel wasn’t exactly well versed on human flirtations and he was often confused when anything of the sort was directed towards him. 

Another time, when Castiel had been beating Dean within an inch of his life all because of some tablet, Dean tried to get the angel to snap out of it by saying, “We’re family. We need you.  _ I  _ need you.” Cupid had actually facepalmed when he’d heard those words, they were so close to ‘I love you’, why couldn’t they have been I LOVE YOU? 

Once, he almost thought he’d been successful, Castiel had said the words, but they’d been cushioned with an “I love  _ all  _ of you” after the simple three words of “I love you” while he was looking  _ directly  _ at Dean. Dean even seemed to be holding back some kind of emotion when he’d heard those words, but whatever he was going to say had been stopped by the rest of that god awful sentence. 

Now, it’s been eleven years. Eleven long, hard, hair pulling, teeth grinding, years, and every time he thought he’d done it, that they’d finally admitted how they felt towards each other, they were interrupted or they stopped themselves at the last minute. The latest evidence of said example was when Dean had prayed to Castiel in Purgatory, saying, “I forgive, of course I forgive you. I’m sorry it took me so long to say it.” Cupid had watched the whole thing, waiting for those three little words, and thought to himself,  _ You know what else has taken you so long to say? I LOVE YOU. Just say it, please, I’m the laughing stock of Heaven because of you two, cut me a break, I just want to go home.  _

This was getting completely ridiculous.

No Cupid had ever failed in a mission before, and he refused to go back to Heaven until he had succeeded, but he had begun to realize that this was not something he could do alone, he needed help, and there was only one person he could ask who was just as fed up with Dean and Castiel’s bullshit, and that was Sam Winchester. 

It was late one night, when Cupid appeared to Sam outside a bar. Sam nearly fell over in surprise. “Sam Winchester,” he said by way of greeting.

“Uh, yes?” 

“Right, yes, hello. I should probably start off by saying that I’m a Cupid.” 

“A Cupid?” Sam repeated, still trying to catch up. 

“Yes, and I need your help.” 

“ _ My  _ help?” 

“Yes. You see, I’ve been assigned your brother’s case-” 

“Wait, my brother?  _ Dean _ ?” 

“Yes, Dean. Now, as I was saying, I’ve been assigned his and Castiel’s case for eleven years and I’m just about ready to go up to Heaven and tell them that it can’t be done. I have never, in all the millennia I’ve been alive, seen two people dance around each other for so long. I need your help, Sam. I can’t take this anymore, you have to help me get them to admit their feelings.” 

“Oh my god. I knew they were destined for each other.” 

“Sam, please, I am  _ begging  _ you, to help me.” 

“Of course I’ll help, I’ve been trying to set them up on a date for the past ten years! With both of us working together, we should be able to swing something.” 

“What would we be swinging, exactly?” 

“Well, Dean and Cas are inside the bar right now, and Dean’s pretty wasted. If we’re going to get anything out of him, drunk Dean is the way to go. Cas on the other hand, even in the state he is now, he’d need the entire bar to get wasted.” 

“Castiel isn’t the problem,” Cupid said. “He’s just waiting for Dean.” 

“Of course he is,” Sam replied with an eye roll. “Well, in that case, let’s go inside and see what we can do.” 

Cupid stayed invisible while following Sam inside towards the bar counter, where Dean was talking to a young woman. Castiel was sitting beside Dean on his other side, staring blankly into the bottom of a whiskey glass.

_ We are not off to a great start.  _

Sam’s abruptness upon re-entering the bar made Castiel look up, confused. “Sam, what’s going on?” 

“It’s nothing to worry about Cas,” Sam replied easily. 

Castiel was still fixing Sam with a curious gaze but with Sam’s dismissive wave he turned back to his drink. 

Cupid watched as Sam moved over to his brother, cutting into the conversation he’d been having with a very blonde, very petite, woman. “Hey!” Dean protested. “I was getting close with that one.”

“Well, I think that you’re barking up the wrong tree.” Cupid almost laughed at that, Sam wasn't wrong. 

“You don’t know that, she seemed into me,” Dean slurred. 

“I also think you’ve had enough for tonight,” Sam said as he pulled a shot glass from Dean’s hand. 

“Whoa, hey! Sammy, what’re you doin’?” 

“Cas!” Sam called.

“Yes?” Castiel asked as he pushed himself away from the bar counter. 

“Watch after Dean while I go get the car.” 

Without waiting for Castiel to object, Sam practically pushed Dean into Castiel’s arms and then rushed from the room, leaving Dean to slump against the angel while he tried to regain his footing. 

“Sorry,” Dean apologized once Cas had put an arm around him to keep him upright. 

“It’s alright, Dean,” Castiel replied with a soft smile, one could even call it fond. 

While Cupid watched Dean’s head fall against Castiel’s shoulder he began to hope that maybe this was finally going to work. 

When Sam returned, declaring that the car was right out front, Castiel helped Dean to the car and Cupid followed, unnoticed. The ride back to the Winchester’s bunker was a short one, and when Dean tried and failed to get out of the car, Sam didn’t lend a hand to help, instead allowing Castiel to pick up the slack.

Sam gave Dean and Cas a wide berth as they entered the bunker. “Get him to bed, Cas, he needs to sleep it off.” 

“‘M fine,” Dean protested. 

“You’re not fine,” Castiel replied curtly. “Now let me help you to your room, you can barely walk.” 

“‘M fine,” Dean muttered again. 

Sam went off towards his own room, but Cupid followed Dean and Castiel down the hallway. Dean really could barely put one foot in front of the other, but Castiel held him up as if he weighed nothing, which to an angel, that was relatively true. 

Castiel turned on the light in Dean’s room and then helped him over to his bed where he gently laid him down. Dean was starting to drift off, the alcohol clearly taking its toll on the hunters body. Castiel slipped Dean’s boots off his feet and set them down on the floor at the foot of the bed before reaching for a blanket with which to cover Dean. 

“Goodnight, Dean,” Castiel said quietly. 

He started towards the door but Dean’s voice suddenly pulled the angel to a stop. 

_ This is it _ . Cupid thought.  _ Please let this be it _ . 

“Stay,” Dean mumbled. 

“What?” Castiel asked, confused, but sounding slightly hopeful. 

“Stay,” Dean repeated.

“Dean, I don’t-” 

“Just c’mere,” Dean said. “Don’t wanna be alone. ‘M tired of being alone.” 

Slowly, Castiel moved towards the hunter until he was standing beside his bed. After a brief moment of hesitation, Castiel kicked off his shoes and then laid down next to Dean. Dean shifted on the bed until he was facing Castiel, mere inches keeping their lips apart. 

Cupid watched with bated breath and crossed fingers. 

“Cas, I… ‘M sorry about how I always treat you. I just… we’ve gotten so close and whenever we start to get closer I… I guess I get scared. But I don’t wanna lose you, I never wanna lose you, Cas. Whenever I do it feels like a part of me is missing.” 

Castiel smiled, a small gummy smile that touched his eyes and lit them with blue fire. “I don’t want to lose you either, Dean.” 

“Kiss me,” Dean whispered. 

Castiel blinked at Dean in surprise. “Dean-” 

“Kiss me,” Dean repeated, louder this time. 

Castiel didn’t wait to be told again, he closed the gap between them and pressed his lips against Dean’s. Both men seemed to melt against each other and when they broke apart, Dean let his hand comb drunkenly through Cas’ hair. 

“You know I love you, right? Don’t think I’ve ever told you that, but I do, I really really really, do. Should’ve told you a long time ago. I love you, Cas.” 

Castiel’s smile was so bright that Cupid almost thought he’d be blinded by it. “I love you too, Dean, more than you could ever know.” 

As Dean slipped off to sleep, happily tucked in Castiel’s arms, Cupid let out a breath of air. 

_ Finally.  _

_ FINALLY.  _

Before Cupid could leave, Castiel turned to look at him. “Thank you, brother.” 

Cupid had forgotten that Castiel could see him and he almost let out a small shriek of surprise, but caught himself at the last moment, instead choosing to offer his brother a smile. “You’re welcome. I know you two will be very happy together.”

With the soft flutter of wings, Cupid left, knowing that after eleven of the most frustrating years of his life, his mission was complete. He returned to Heaven singing the praises of Dean Winchester and Castiel. He was greeted with the sound of bells as all of Heaven rejoiced in one of the most important unions in all of angel and human history.


End file.
